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$138+ Cheap flights from Calgary (YYC) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
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Cheap flight deals from Calgary to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$223
(Delta)

One-way from

$138
(Delta)

Popular in

December

Cheapest in

May

Average price

$205
Provider with most accurate pricing for Calgary-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Calgary-Chicago Midway flights.
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From Calgary to Chicago Midway
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One-way flight from Calgary to Chicago Midway
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Highest demand for flights based on searches. 19% potential increase in price ($73 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Calgary to Midway

Cheapest flights from Calgary to Midway
Explore the most affordable flight options available from Calgary to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 30, 2025.

This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/266:30 amYYC - MDW
1 stop5h 45mDelta
Mon 6/29:20 amMDW - YYC
2 stops14h 41mDelta
Deal found 4/28$223
This Kissandfly.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/76:30 amYYC - MDW
1 stop5h 45mKLM
Sat 5/101:55 pmMDW - YYC
1 stop7h 45mKLM
Deal found 4/28$291
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/137:00 amYYC - MDW
2 stops15h 18mMultiple Airlines
Mon 6/166:20 amMDW - YYC
1 stop14h 45mMultiple Airlines
Deal found 4/28$346
This Mytrip deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/277:55 amYYC - MDW
2 stops23h 50mPorter Airlines
Tue 6/39:40 amMDW - YYC
2 stops12h 44mPorter Airlines
Deal found 4/28$455
This Kissandfly.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/712:30 amYYC - MDW
1 stop8h 10mWestJet
Sun 5/111:55 pmMDW - YYC
1 stop7h 45mWestJet
Deal found 4/28$558

Cheapflights Fare Finder

Customize your flight search to find flights from Calgary to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 30, 2025.
Use the filters below to find and compare flights from Calgary to Chicago Midway Airport that are best for you.

Fly from

Calgary

Fly to

Midway

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 5/26

6:30 am-1:15 pm

1 stop5h 45m

Chicago Midway

Mon 6/2

9:20 am-11:01 pm

2 stops14h 41m

$223

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 6/13

7:00 am-11:18 pm

2 stops15h 18m

Chicago Midway

Mon 6/16

6:20 am-8:05 pm

1 stop14h 45m

$346

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 5/27

7:55 am-8:45 am

2 stops23h 50m

Chicago Midway

Tue 6/3

9:40 am-9:24 pm

2 stops12h 44m

$455

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 6/1

7:00 am-9:27 pm

2 stops13h 27m

Chicago Midway

Mon 6/2

9:20 am-6:40 pm

2 stops10h 20m

$642

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 5/26

6:30 am-5:45 pm

1 stop10h 15m

$138

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 5/26

9:15 pm-10:14 pm

2 stops23h 59m

$174

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 5/21

7:55 am-8:45 am

2 stops23h 50m

$213

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 6/11

1:00 am-6:02 pm

2 stops16h 02m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Compare providers for flights from Calgary to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Calgary to Midway in April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Calgary-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Calgary-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Calgary-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Calgary-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Calgary-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Calgary to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Calgary with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Calgary to Chicago Midway Airport

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated April 30, 2025.
To help decide which airline to fly from Calgary to Chicago, see what other customers have to say about Porter Airlines, Delta and WestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
285 reviews

Food

7.6

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews

Food

7.6

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,936 reviews
Porter Airlines
8.0
Very good
285 reviews

Food

7.6

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,826 reviews
Porter Airlines
8.0
Very good
285 reviews

Food

7.6

Boarding

8.2

Overall

8.0

Comfort

8.1

Crew

8.8

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

Related info for your journey

Find useful and relevant information for your journey from Calgary to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Calgary to Chicago Midway?

    For a flight from Calgary to Chicago Midway, you will be flying from Calgary. Calgary (YYC) is just 5.8 mi from the center of the city. Calgary is the only Calgary airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Calgary on a regular basis.

  • What are the cheapest airlines flying from Calgary to Chicago Midway Airport round-trip?

    Our cheapest airline available from Calgary to Chicago Midway Airport is Delta. Our recent data shows that you can find tickets from as low as $223 on this airline. Additional options worth looking into are Porter Airlines and WestJet, starting at $455 and $642 round-trip.

  • What are the cheapest airlines to fly from Calgary to Chicago Midway Airport one-way?

    $138 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Porter Airlines and WestJet, with prices starting from $213 and $326, respectively.

  • Can I find deals for flights from Calgary to Midway that include hotel bookings?

    Yes. In addition to deals on Calgary to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to Midway.

  • Can I find deals for business class flights from Calgary to Midway?

    Yes. Cheapflights offers flight deals from Calgary to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Calgary to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Calgary to Chicago Midway Airport (average of $160). Flying from Calgary to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Calgary?

Book flights to Calgary if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
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Valparaiso
Chesterton

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